How I Met Hollywood
by WikiSalvatore
Summary: Elena Gillbert is offered the job of her lifetime! As a personal assistant of one of Hollywood's biggest A-Listers, Damon Salvatore. Will they be able to keep their relationship from becoming too personal? Or will they not be able to resist the feelings they have for each other? Elena/Damon, Elena/Stefan, Caroline/Klaus, Caroline/Stefan, Stefan/Lexi
1. Chapter 1

**Chapter 1 **

As soon as my eyes opened I remembered today was the day when I finally make my big step in the film industry. I got the job of being a personal assistant, to the one and only, Damon Salvatore. From what i heard, he is the kind, gentleman type. And did I mention he is the HOTTEST man that has ever walked on earth? Now you know why I am excited.

I quickly got out of bed and walked to the closet. I took out my white blouse and black peplum skirt and made my way to the bathroom where went about my morning routine. After having a quick brekfast, I found myself on my way to the Warner Bros. Studios, but first I had to stop by starbucks to order my usual Iced Vanilla Latte. 10 minutes later i was walking into reception where I was greeted by a red-haired receptionist, Stephanie. 4th floor was where I was now heading.

When i walked out of the elevator I was met by a medium height, dark haired girl.

'Hi! You must be Elena! I'm Jess, Mr Salvatore's past assistant. Follow me and I will take you to his office.' She really reminded me of Bonnie, my best friend. Bonnie is still living in Mystic Falls with my brother Jeremy. She was always the one for small town life. Me however, I wanted more than a little town, I want to be a movie director. Hence the reason why I am standing by my new work space.

I sat down and turned on my laptop. I was still waiting for my boss to finish off some meeting. Jess told me all about my responsibilities, gave me Mr Salvatore's schedule and taught me all I need to know before leaving the office. I was just checking my email when a girl walked up to my desk.

'Hi! I'm Caroline!' The blonde greeted me.

'Hi, I'm Elena. Do you work here too?' I asked politely, she seems nice.

'Yeah, I am one of the Casting Directors. You must be Damon's new assistant?'

'Yep, and I am totally petrified. Do you want to grab lunch with me later?' I might as well make a new friend!

'Sure! I will come by your office at like 1pm. By the way, there is nothing to be scared of, Damon doesn't bite!' She laughed and I couldn't help but join her.

**A/N - Thank You for reading! Please review so I can improve the story! **


	2. Chapter 2

**Chapter 2 **

After having my lunch with caroline I returned to my desk and finished off some work I had left over from the morning. Caroline is proving to be a great friend material, her and Bonnie would get along so well. We had lunch at the cafeteria, we talked all about our past, plans for the future and we have a lot more in common than i thought! Caroline's dad's sister is actually the sheriff at mystic falls! Caroline even lived there for a couple of months while her parents were getting divorced. Shame we never met, I think we would have been good friends! I was pulled out of my daydream by the office door opening.

Now, there are two types of girls in this world. The ones who panic when they see a celebrity and can't say a thing and those who go into talking overdrive mode. Lets just say I am one of the ones who just start talking like mad.

'Mr Salvatore! It's great to finally meet you! How was the meeting? Do you need anything? Oh, sorry where are my manners! I am Elena Gillbert, your new assistant!' Talk about embarrasing... He just chuckled at my sudden burst of words.

'Welcome to Warner Bros. ! Could you please get me a Cinamon Dolce Latte? I will be in my office.' He is a lot more polite than i imagined him to be.

'Of course!' I replied. Whoah, his eyes are gorgeous...

'Thanks' He flashed me a quick smile before heading to his office.

After picking up his coffe, I gently knocked on the door. He responded with a simple 'come in' and so I did. I placed the coffe on his desk and asked if he needed anything else.

'Could you please book me two tickets to the Dolce &amp; Gabanna fashion show next friday? Katherine is forcing me to go even though I told her multiple times that I hate watching Fashion Shows. They bore me to death.'

'I will go do that now, I also want to remind you that the metting with Mr Mikaelson starts in 15 minutes' I answered. I have 2 hours of work left, so I quickly book the tickets. Katherine Pierce is another one of those people who slept their way into show-buisness. I swear all she does is turn up to events and fashion shows, smile and that's why everyone loves her. She has dated all the important people in the industry, I guess Damon is her current victim. It's just a matter of time before she moves on to the next young star.

When 5pm came, I grabbed my purse and my coat and made my way to my car. Tonight I was supposed to meet Matt, we have been dating for quite some time, but he had to stay behind at work. I guess I will just order a take away and spend my evening in bed. That's what I did.

**A/N - I have all day at home today, so I think there might be a couple more chapters posted! Please review so I know how to improve!**


	3. Chapter 3

The rest of the week passed in a blur. Today is Friday and tomorrow I am heading to Mystic Falls, my aunt Jenna and Alaric just had their baby girl. Hopefully, i can spend some more time with Bonnie and Jeremy. It feels like I haven't seen them in forever! Well, it is kind of true, I don't visit often. Anyway, back to reality.

After having a shower and getting myself to look presentable, I made my way to this little café where I was meeting Caroline. We really hit off, I invited her to come to Mystic falls with me. She said she would love to go and I can't wait to introduce her to Bonnie!

'Elena! I ordered you a coffee and a bagel, like always.' Caroline said as soon as I walked through the door.

'Thanks! Apparently, Matt is going somwhere with Tyler, so he can't make it to Mystic Falls. "

'Well, you can't really blame him for making excuses. From what you told me, that town only holds bad memories for him. ' she did have a point, Matt's sister died, shortly after his mum leaving them all alone. I understand why he didn't want to go back.

Shortly after, we left the café and went to work. Mr Salvatore was on set today until after lunch so I wasn't that busy. He took a couple of interns with him so I didn't have to come along. While I was filling out some paperwork, a VERY handsome man entered the office. His forest green eyes stared right into mine.

'Is Damen here?' He asked casually. It took me a couple moments to peel my gaze off him and think of a reply.

'Ummm, no. Do you need me to pass him a message? Or do you want to come back later? He should be here in about 20 minutes or so.' Why is he staring at me! Oh my god Elena, calm down you are just talking!

'I think I will wait, I'm Stefan Salvatore, Damon's brother.'

'Im Elena. Do you want anything?' Since when does Damon have a brother? Anyway, I guess the good looks run in the family.

'Coffee would be great." So I made two coffees and walked back into the office. Stefan made himself comfortable on one of the plushy chairs. I passed him one coffee before sitting back down at my desk.

'So, you are my brothers new assistant?'

'Yes. Mr Salvatore hired me last week. '

'I hope he isn't overworking you too much. Beautiful woman like you should be getting all the work done for them!' He flashed me a smile, while I felt a blush slowly appearing on my cheeks.

'Of course he isn't! He has been a great boss.'

'Aww thanks Elena!' Damon said as he walked into the office. 'Brother! What are you doing here?'

'Well I have some things to talk to you about..' Stefan replied with a serious tone.

'Okay, come into my office.' Damon's eyes filled with worry.

A/N- It was great to see some of your comments on this story! I plan on this to be at least 30 chapters long!


	4. Chapter 4

I never found out what was going on between Stefan and Damon. It's not like I can just ask! Anyway, today me and Caroline are leaving to Mystic Falls! I am so excited! I also get to meet my baby cousin. Who still hasn't got a name beacause Alaric and Jenna want it to be 'extrodinary'.

Me and Caroline where 1 hour into our journey when I got a unexpected phone call.

'Who is it?' Of course Caroline needs to know.

'Umm, its Damon..' Why is he calling me? It's a Saturday! 'Hello?'

'I really need you right now!' He said with a slight panic.

'Well, I am an hour away from Hollywood. What is it you need me to do?'

' I need a date for that stupid Fashion Show..' I bursted out laughing.

'I will send Katherine a message to remind her.' He really is a good actor, I actually thought it was urgent.

'No Elena! Katherine run off to California for some stupid party and left me to attend that show. However, they expect me to bring SOMEONE, so as my personal assistant.. I need you to come with me. '

'No way! I am not going with you to a Dolce &amp; Gabbana fashion show! '

'Elena please! I am your boss!' There is no way I would go to a place like that with my BOSS! Can't he just grab a model from his speed dial?

'Well Mr. Salvatore, as your assistant I am not going to attend that event. Just phone up some model and pretend she is your friend' Why is he calling me anyway, does he think we are friends? Are we? Ugh Elena stop it!

'Elena if you don't get your ass here, the I WILL fire you!' Okay, now I don't know if he is joking..

'Fine!'

'Great, well you have 4 hours until you need to meet me at my house. I will tell Marcus to get you something to wear and get some people for your make up. Meet me at my place at 2! Thank you, you are my saviour!' And he hung up.

What did I just agree to?

A/N - I know it's a bit short but I wanted to do all the fashion show stuff in the next chapter!

What should Jenna's and Alaric's daughter be called? I also want to thank you all for those amazing reviews, they make my day!


	5. Chapter 5

As soon as I arrived at my place, I was constantly interrupted by the door bell. In the matter of 20 minutes, my whole apartment was filled with people. Hair stylists, make-up artists... And some people that delivered my outfit for tonight.

At first the situation was so overwhelming that I completely forgot to even look at the dress I was going to wear. That was until Caroline reminded me that i was yet to see what was hidden in the black garment bag.

'Come on Elena! Aren't you even curious to see that dress?' Caroline asked.

'The dress! I completely forgot!' I replied while heading towards the bag that has been resting on my bed. I slowly un-zipped the bag. Inside was a beautiful red gown. It must've cost a fortune, it was Donna Karan! That is one of my favourite designers.

'It's beautiful..' Caroline expressed. Our little moment only lasted a short while as I was soon pulled over to get my hair and make-up done.

I was smoothing over my dress when Caroline walked in, holding a silver box.

'Here. These will look great with the dress.' She said as she pulled out gold earings with little ruby crystals. I quickly put them on and made my way towards the mirror. I was shocked by what I saw. I actually looked beautiful, the dress looked perfect on me. I smoothed my hands across the dress once again, while making my way towards the door.

'Have fun, and make sure to tell me how it went!' Caroline said as I made my way out.

'I sure will!' I replied and walked towards the limo where Damon was standing.

'Good evening Mr Salvatore.' I said. His mouth fell slightly open when he saw me but he quickly recovere.

'Elena, you look stunning!' He smiled

'Thank You, you don't look bad yourself.' He really didn't. He was wearing a black tux and his hair was all over the place like always. And those ocean blue eyes.. Ok, I need to stop before I start drooling.

'Well, lets get going.' He held the door open for me like a real gentleman.

The ride there was very entertaining. I never really had the chance to have a proper conversation with Damon. He was a lot more, down-to-earth than I imagined.

'Just to warn you, we have to walk down the red carpet. All you need to do is smile, I will take care of the questions. They will probably assume we are a couple but I will take care of that.' Now I was getting panicked.

'I shouldn't have came! They will make up stupid rumors about you now!' I replied.

'Don't worry, they know I am with Katherine.' Why did I agree to this..

'Okay lets go!' As soon as the door opened, we were met with loads of flashing lights. We quickly made our way to the building, thanks to the bodyguards, who helped us through the paparazzi. We stopped for some photos, it was a lot more fun than i expected. After sticking some poses we made our way to our seats.

The fashion show went by as a blurr. I couldn't really concentrate when I was sitting next to the hottest man on earth and the whole room was filled with celebrities! After the show came the after party. That was when all the action started.

'Elena, this is Robert Pattinson.' Damon was just introducing me to my favourite actor ever, when we were rudely interrupted by a tall brunette.

'Damon! I haven't seen you for ages!' She purred, I instantly disliked her. She seemed like another one of those Katherine-like celebrities.

'Isobel..' And it seemed like even Mr Salvatore wasn't one of her fans.

'Who is she?' She asked, giving me a dirty look. I just wanted to punch that woman in her powdered little nose.

'Elena Gilbert. Nice to meet you' I replied in a cold voice.

'Well Damon, I guess you run out of other dates. She isn't exactly your type.' My blood boiled. This is exactly why I didn't want to come here with HIM.

'Isobel! Have you got any manners, or has that stupid reality show really brain-washed you?' Damon replied angrily.

'Excuse me..' I quickly walked away in the direction of the toilets. After I cooled down and returned to the party, Damon was no where in sight. So I made my way towards the bar instead 'A Tequila, please'

'Make that two' A warm voice said. I turned to face the man and was met by a pair of forest green eyes.

'Stefan, what are you doing here?' I was very suprised by his presence.

'Oh, you know. Fashion show after parties are my favourite.' He laughed gently.

'Well, I'm glad you are here. It is nice to have someone to talk to.' We continued to have a great conversation, that man really knew how to make me laugh. And then one Tequila shot turned into 2 and then into 4. I was still able to think clearly but Stefan. Probably not, because the next thing he did was leaned in towards me a quietly whispered into my ear.

'You look beautiful tonight. I am sooo jealous of my brother right now.' His voice sounded so mesmerizing. However, I quickly remembered why I am here.

'Stefan, this is not right. You are drunk..' I tried to push his hands, which were now making their way up my leg, off. However, his grip just tightened. I was starting to panick, my heart sped up. I couldn't cause a massive scene in front of everyone. I tried to push him off me once again but he just continued.

'Elena, I know you want to..' His sentance was interrupted by a strangers fist colliding with Stefan's jaw. That stranger turned out to be my boss.

'Are you ok?' He asked worried

'Uhhh... Yeah...I'm fine' I was so shocked. Stefan seemed a lot more sensible than that. He was still recovering from that punch.

'Come on, lets get you home.' So we made our way back to the limo. ' I am so sorry about my brother. He wasn't himself, it was all the alcohol...'

'It's fiine Damon, really.' I replied.

'I guess I know why he acted like that, you do look amzing tonight.' He gave me a crooked smile, while my cheeks were warming up.

'Thank you.' We were just outside my apartment when Damon leant in and kissed my cheek.

'Thank you for coming with me tonight. I will see you on Monday, have a good weekend.' He said gently.

'You too.' My skin was still tingling from where his lips connected with my skin.

Such a shame he was my boss...

**A/N - Im so sorry for the long wait! The story is finally getting somwhere with Elena and Damon! What do you think about Stefan's actions? I am still waiting for some suggestions on what I should name Alaric's and Jenna's baby girl! **


	6. Chapter 6

I am so sorry for the long time it took me to update! I was very busy lately and I completely forgot about this story! Did anyone else go through like 10 packets of tissues while watching the season 6 finale? Because I sure did!

The next morning...

I woke up at to the sound of my alarm. Apparently it was 6 am already. I had to fight my eyelids all the way to the bathroom, where I had my shower and got ready. I had a couple minutes left so I decided to grab myself a quick muffin from the cupboard. For the first time today I had some time to re-think yersterday's events. What I concluded was Stephen was either REALLY drunk or has feelings for me. I am not too sure what I feel towards him anymore. I used to think he was a gentleman and all, but judging from what he did last night, he is a douche. My thoughts were inturrupted by a text from Caroline stating that she was waiting for me down stairs. I was ready to start our little road trip.

DAMON POV

'Baby we will be late!' This woman can drive me crazy sometimes. Why does it take so long to put on a pair of jeans, throw on a t-shirt and leave the damn house? Another 5 minutes passed before Katherine finally emerged from our room. Obviously not dressed in the outfit I just described, instead she was wearing a long red maxi dress and a pair of black heels.

'Alright Mr Impatient, I'm ready to go.' She payed me a quick glance before grabbing her purse and walking toward the door. Remind me again, what was I doing with this girl? Oh yeah, apparently there had been no-one else to fall in love with. It just had to be Katherine Pierce. Don't get me wrong, she is one of the most beautiful women out there, her long brown locks framing her big brown eyes, making them nearly irresistable. Together we make a great couple, in the Hollywood lights at least. She has also always been there for me, since my mother died. My mum was the most caring person in this world, but she passed away 3 years ago due to a car accident. I was devastated. Drowning all my sorrows in glasses of bourbon, until she came along. You could say Katherine was my saviour. I know people think of her as a gold-digging bitch, but she is different. Underneath the mask she puts on everyday is a small town girl who lost her family too young. Brought up in a home full of fake family drama, all put up for the sake of reality tv would do that to a person. Her whole life she had to put on the mask in front of the camera, but to me she is different. We love each other.

'Kathy, where would you like to eat today?' I asked putting on a small smile.

She thought about it for a while, then replied ' Maybe that Italian place we went to last week? I fancy a nice salad.' Of course she wanted to go there. It was one of those places where the food they offered you contained less than 100 kalories. Horrid if you ask me.

'Sure. To Mulino, please. ' I told the driver.

'Oh yeah Damon, my step mum asked me to appear on her new TV show, again. I will need to leave for a couple of days. Unless you would like to come with me?' She proposed, but I know she secretly wanted me to stay. She always thought of these trips as times where she can free herself from our relationship and relax a little. I wasn't about to take that away from her.

'Nah, I have some more stuff to do before leaving for Australia. Are you sure you don't want to acompany me on that trip? I will be gone for a long time?' We started shooting for my new movie soon, which reminded me that I need to ask Elena is she could come. I need an assistant while I am there.

'I have some stuff to do here. I will try my best to visit though, will you really miss me that much Damon?' She asked with a smirk.

'Oh yes, I definately will' I replied with a smpile befor leaning in and placing my lips on hers. She quickly granted my tongue the access and deepend the kiss. Her soft lips tasted of coffee and cinamon. Before we could get any further we were already at the restaurant.

Elena POV

'How long 'till we get there?' Caroline asked for the hundreth time.

'We are nearly there, a couple more minutes' We were already in Mystic Falls, on our way to my parents' house.

'Well Elena, I know you are not telling me something. And I know it's bugging you, you have been VERY quiet.' Oh no, I didn't want to tell her about Stefan. She has been crushing on him for so long. However, I knew she would never stop asking.

'Stefan tried to kiss me.' I blurted out.

'Stefan, WHAT?' She repeated with wide eyes.

'I am so sorry Caroline! I think he was just really drunk. We both had a lot to drink. I obviously stopped him before he could even get close enough to kiss me but he tried. I tried to push him off but he just kept going! Then Damon punched him straight in the face. Im sorry Caroline..' I could see how devestated she looked.

'Don't worry about it Lena. It's fine..' I know she was lying but I had to drop the subject as we were parked outside my family home. We made our way to the door carrying our suitcases. I knocked on the door gently.

'Elena! You're here!' My mums voice filled my ears as she wrapped her arms around me. After what seemed like a long time, she released me and turned to Caroline.

'Oh and you must be Caroline! Oh my gosh you are so grown up, the last time I saw you, you were just a little girl!' My mum repeated what she did to me before taking us inside the house.

After greeting my dad and brother, we changed an made our way to the Mystic Grill where we were meeting Bonnie, Tyler, Matt, Klaus and Rebekah.

'Elena!' The whole table shouted at my sight. I could not help but laugh at them.

'Wow, it is so good to see you guys! This is Caroline.' I introduced my friend.

'Hello Love.' That is when I saw the way Klaus and Caroline looking at each other. It wasn't any way. There was something between those two, I think we could all see it because all eyes darted towards them.

The rest of the evening passed in a blurr. We were having so much fun that I completely lost track of time. Caroline and Bonnie hit off so well that we ended up having a girls night at my house. I missed Bonnie so much, we were friends since the sandbox and nothing could tear us apart. Even the distance between Mystic Falls and Los Angeles.

A/N - I will try to update as soon as I can! I feel like the last couple of chapters have been a bit rushed so I tried to take as much time on this chapter as possible. I didn't want to portray Katherine as a complete bitch, but trust me, Damon thinks too higly of her! Hope you enjoyed the chapter!


	7. Chapter 7

The next morning, I woke up to the familiar smell of blueberry pancakes. Careful not to wake up the girls, I made my way to the bathroom that I once had to share with my brother. It felt really good to finally be back at home, even if it was for a little while . I wished we could stay longer but tomorrow was my first day without Jessica. I was officially going to be the secretary of Damon Salvatore.

My thoughts were interrupted by Caroline joining me in the bathroom. We both did our make-up in silence; she wouldn't talk to me much since I told her about Stefan.

'Alright Caroline, I had enough. You are one of my best friends! I hate to see you like this, it wasn't my fault.' I paused, not really knowing what to say. 'I am sure Stefan didn't mean to kiss me. He just had too much to drink, no feelings!'

After a couple of moments she finally replied, ' I am sorry 'Lena. It's just hard, I have been trying to get Stefan to notice me for MONTHS. All you had to do was turn up and he pounces on you!'

'Come on, lets get downstairs and eat brekfast. Bonnie should be up any moment.' I replied, relieved our conversation was brief. I did not want to feel guilty for the rest of the day. We made our way down the stairs, having a small conversation about our plans.

'Good morning, pancakes are on the plate. Grab some and join us in the garden, it's such a great day today!' My mum was always like that. Cheerful. No matter what, she could always stay positive. She was the best role model someone could have. She was always there for me. We just finished eating when my dad started speaking.

'Elena, I found some boxes with your stuff last time I cleaned the attic. I will place them into your room, I'm not sure what you would want to keep.'

' I will sort that oout before we leave for the party.' The Mikelson's are throwing a big barbecue today. It used to be my favorite party of the year, that was before I broke up with Elijah and things just got too awkward. It has been a long time now, so I hope we will avoid any embarrassing conversations. After breakfast was finished, Bonnie took Caroline shopping, I stayed behind to sort those boxes.

They were mainly all trash, but I found some of my old journals and a book. It wasn't any book though, it was filled with songs. See, when I was younger I used to really enjoy singing and playing the piano. Then I discovered my love for directing and forgot about music. Until now. I could not help but flick through the pages, some filled with romantic pop songs and some a lot more serious. One caught my attention in particular, it used to be my favorite. I couldn't help but remember the tune. Quickly, I was brought back to reality as I heard Jenna's voice downstairs. Rapidly, I sped sown the stairs, wrapping Jenna in a hug as soon as I saw her.

'Aww, Elena! I missed you big girl!' Jenna spoke with a sweet voice.

'Me too! Rick, you look great. Where is that little baby I can't wait to meet?' Then I saw the little baby sleeping peacefully in her car seat. She was a little sweetheart.

'Well Elena, meet Hayley Eve Saltzman!' The little girl was a mini version of Rick, apart from the little blonde locks she must've inherited from my aunt. 'She is a little beauty.'

'Come on, you can hold her!' Jenna passed me the little girl, who was now starting to wake. She was so small, I was afraid of crushing her. In the same time, she was so soft and warm. I can't wait until I have my own kids one day. I have always wanted a big family, but it won't happen anytime soon. It's not like Matt isn't father material. He is the most caring person I have ever met! I just can't picture myself marrying him one day, he isn't meant to be my forever. He proved that by not wanting to come with me too Mystic Falls. When we were still teenagers, I was so deeply in love with him, but lately we drove apart. I haven't seen him for days, last time I spoke to him was over the phone at 10pm. We don't have the time. I hope I will meet the one soon enough. In that moment I made the decision that i need to talk to Matt. Soon.

A/N - So guys, the next chapter is the barbecue and coming home! Hope you enjoyed...


	8. Chapter 8

We never made it to the barberque that night, Caroline got a phone call regarding her mum. She fainted at work and was taken to the hospital immediately. They run some tests but nothing is clear yet, so as expected we quickly made our way back to Los Angeles. As soon as we arrived at the hospital, we were taken to Mrs Forbes' room.

'Mum, oh my god, what happened? Are you okay? How are you feeling?' Caroline was panicking, she loved her mother more than anything and couldn't afford to lose her.

'Don't worry Honey, I will be fine. I was probably just overworked. Everything will be fine. How was your trip girls? How is Miranda doing, we haven't seen each other since that hell of a divorce..' She said sadly.

'She is doing great, they are coming down to LA soon, you have to meet up! I will go get some coffee, do you guys want any?' She said in an attempt to give them some time alone.

'Sure' Caroline answered.

I made my way down the hall to the coffee machine. All of a sudden my top got soaked in warm liquid. I gasped and said, ' For goodness sake, can you not watch where you are going?' My white shirt now covered in brown stains.

'Im sorry! I wasn't looking..' The man replied guilty. I was working on trying to wipe off the coffee when I finally acknowledged the man standing next to me.

'Elena?' The man asked.

'Damon? Sorry, I didn't mean to be rude or anything!' I was truly embarrassed, I just shouted at my brand new boss.

'It's fine, I was the one who stained your shirt.' He replied chuckling slightly.

'What are you doing here, if it's okay for me to ask?' I was curious to know why he was in a hospital.

'Im here with Katherine, we just found out she is pregnant.' He said slightly sadly.

'Wow! That's great, congratulations! Should I call your publicist, let them know or would you rather prefer to keep it quiet?' I was so happy for him, but couldn't help but feel a little bit of jealousy. They will have the most gorgeous babies.

'Thanks, I guess.. I think we should keep it quiet for a while. Im a bit terrified at the moment, need some time for it to sink in.' He replied looking dazed. His eyes seemed a bit thoughtful.

'Well, congrats again but I need to get back to Caroline. See you tomorrow!' I made my way back to the room, our little run in made me forget the coffee...

I was back at home later that evening, after washing my top I cooked myself some Spaghetti bolognese and put on the Notebook. I was just starting to tear up when my phone went off. The screen revealed it was Matt.

'Hi' I breathed out.

'Lena you okay? Have you been crying?' Matt asked worried. I laughed slightly before responding, 'I was watching the Notebook again. It always gets to me. ' I paused before continuing, ' Listen we need to talk, maybe you could come by tonight?'

'Yeah, sure. Im on my way, be there in 10.' I think we both know it was time to end things. We haven't been talking lately and we are too busy fir our relationship. I will still love him, whatever happens but our love is more like sibling love live rather than romance. I want to start a family, but not with Matt.

A/U- I wasn't planning on making Katherine pregnant but I think it is needed for the story to progress faster. I can't wait to start writing all the Delena goodness!


	9. Chapter 9

Damon POV

I didn't know what to think anymore. Me and Katherine haven't been together in a month. This baby is 3 weeks old according to the doctor. That would mean it's not mine. But Katherine denies anything to do with her cheating. My mind was racing with thoughts.

'Mr Salvatore, your brother is here.' Elena said.

'Let him in.' I replied dazed. I called him to my office to confine in him.

'You wanted to see me?' He said walking in. His eyes were racing around the room nervously.

'Sit down.' I told him before pouring us some bourbon. 'Katherine is pregnant.' His eyes quickly flashed some panic before he regained his composure. I frowned at his reaction.

'Congratulations!' He said before putting on a smile, that didn't quite reach his eyes.

'Is everything alright? You seem stressed about something.' I asked with worry.

'Umm. Just some work problems, you know..' He replied 'How far along is she?'

'Three weeks.' Three damn weeks i wanted to add, 'which means she cheated on me. Or the doctor was wrong.. We haven't had sex in a month Stefan! She cheated on me and got herself pregnant. I will kill that bastard who she slept with. I loved her! It could have been our baby...' I whispered.

'Im sure it will all work out, listen i got to go, see you soon.' With that he walked out of the door leaving me with my glass of bourbon.

Elena POV

After Matt arrived, we got comfortable on opposite sides of the couch. None of us wanting to start this conversation, so i took matter into my one hands.

'Matt I love you, but It's not enough. we have been so distant lately, we barely see each other, we never have the time to talk. Our relationship is so badly damaged that I don't have the will to fix it.' He just stared at me while I spoke it all out, ' it might seem like I'm giving up but I just want to start my life, start my own family! You don't want that, but I don't want to wait any longer. I've waited 2 years for you to catch up, however you are still too caught up on parties to call me! Im ready for a relationship where I can move on with a good life. I'm sorry but I just can't stay with you any longer. Im so sorry Matt..' I looked up into his teary eyes and couldn't help the sob that escaped me.

'Elena I love you! You are the one, we can make this work! I will move on, we can move in together, hell we can have a baby! I want you Lena!' He replied.

'No Matt, no! I had to threaten you with a break up so that you agree on moving in together! Don't you see it? I want to move on!' I cried out.

'I think you should think this through, I will see you tomorrow. Please just think about it.' He said before walking out.


	10. Chapter 10

'Katherine, why did you lie to him? He deserves the truth!' I shouted at her.

'I love him, he will be the father of our baby. It doesn't matter it's yours, you don't want it!' She screamed back before hanging up.

Elena POV

'Elena can I speak to you?' Damon asked through the phone.

'Sure.' I walked into his office.

' Did the coffee stain come off or do I owe you a top?' He joked.

'Well you're lucky, it came off.' I replied.

'So back to business, are you able to come to Italy? We start filming Midnight In Venice in a week and I need to know if you will be able to assist me?' We spoke about this a couple days back, I said I have to double check if I'm not needed in LA for other businesses but my schedule is clear.

'Yeah, I prepared everything for Stefanie to take care of while we are gone.' Stefanie is a new intern, she will stay here while I go with my boss to help out on set.

'That is great, now the pay will be 10,000 dollars a week as you are going to be abroad and wont have as much free time as in LA. I hope that is okay?' I stared at him with my mouth hanging open.

'10,000 dollars a week, seriously? That is loads!' I replied shocked. We will be gone for four weeks, that is 40,000 dollars. I do need as much money, my savings are running out. That would be able to pay off my apartment.

'Well, you will probably be working 7 days a week. Obviously your evening will be clear, oh I forgot to mention.. We will be staying at a mansion I have got in Italy.' He said casually.

'We?' I replied a little dazed.

'Yeah, me, you and some friends of mine who have a part in the movie.' He said. Now I was scared, I will be in a house full of famous actors.

'Who are those friends exactly, if I can ask?' I asked curiously.

'Bonnie Bennet, Enzo Malarkey, Rebekah Mikaelson..' I stared at him wide eyed. Yes, Rebekah is related to Klaus and Elijah, but I never met her. She started acting in her teens and left Mystic Falls shortly after. She does keep in contact with her family but rarely visits. Those three names are the biggest actors in Hollywood right now. I was going to spend four weeks living with them? And to top it off with Damon, the oscar winning movie actor and producer? I have to tell Caroline, she will freak...

I was at home when I got a phone call from Care.

'Elena can you get to the hospital?' She asked me in a shaky voice.

'Sure, I'm on my way now.' I took off in my car to the hospital. I hope Liz was okay, Caroline seemed very sad. She couldn't lose her mum now, she just lost her father. He came out gay, got married to a man he was cheating with and left. No one knows where to.

'My mum fainted again, they took her for a MRI scan of her brain.. They suspect cancer. Brain Cancer, Elena I'm so scared... I don't want her to leave me!' She cried. I grabbed her into a tight embrace and cried with her. Later that night the doctor came back with the results. Liz Forbes had stage 3 brain cancer. She had a couple of months left to live..

A/N- Lots of confusion over the pregnancy, don't worry everything will get solved in the next couple of chapters!


	11. Chapter 11

Liz was released from hospital a couple of days later. Her and Caroline left to spend the rest of her time at their lake house in Virginia. I was finishing packing my suitcases when I heard a knock on the door. I walked up to it and opened the door enough for me to look who it is.

'Matt, I told you I am moving on. You should do the same..' I said through the small gap.

'But I don't want to move on.. Please Lena. Let me in!' He seemed weird, different.. He pushes the door open further and pinned me against the wall. He pushes his lips to mine and I knew what was wrong, he was drunk.

'Get off of me Matt!' I shouted pushing him off.

'I love you! Why don't you listen to me, fuck sake Elena!' With that he stormed out of the apartment. I locked the door and made my way to bed. Tears staining my cheeks.

Damon POV

'Just tell me the fucking truth Katherine! Who's baby is it? I know it's not mine!' I shouted losing my patience.

'Does it matter? You will raise it like your own because you love me, right? I want this to be our family! Please.. Please Damon.' She spoke sweetly.

'Are you out of your damn mind? You cheated! Slept with another man, got knocked up and want me to clean up your mess? The only reason you want me to pretend that this is my kid is because you are afraid of the press! You know they will ruin you when they find you are a cheating whore Katherine. Don't worry I won't spread gossip about you, I will leave it up to you to explain how you cheated and got pregnant. Your career is over, just like our 4 year relationship.' With that I left to my study. The only thing I wanted to know, is who she deemed more important than our relationship.

'By the time I'm back from Italy, I want your stuff gone. You can take the guest bedroom.' I said sternly when she walked into the master bedroom later that night.

My eyes wandered across her small stomach, you could just start to see a tiny bump on her always perfectly toned stomach. It disgusted me. I couldn't look at it without thinking of it as the proof of her infidelity. I tore my gaze away and looked at her face. She must have been experiencing morning sickness as her face was pale as a ghost. However, I cannot feel any sympathy. All I feel towards her is disgust.

A/N- Who do you think is the baby daddy?


	12. Chapter 12

Elena POV

Damon's private jet was all ready to go, I made sure before I boarded my own plane. I wish I could fly first class but economy class is what I have to take right now. We were ready to take off when a flight attendant spoke, 'Miss Gillbert?' I looked up before replying, 'that's me, is everything alright?'

'You have boarded the wrong plane. Come with me I will take you to the right jet.' She said with a fake smile.

'But I'm sure this is the right plane... Im travelling to Florence.' I replied.

'Your ticket has been changed and you are to be flying in a different plane. Your baggage is being transported too.' I stared at her wide eyed before following her. Who would have changed my ticket, who was allowed to do that? We arrived at the plane, I scanned my eyes across it and spotted small writing that read 'Salvatore'. Damon. Of course. He is making me fly with him in his private jet. We boarded the plane and I looked around. Letting my eyes take in my luxurious surroundings, there was two sofas on either side of the cabin, a bar in the corner and a massive tv in the other.

'You like it?' Damon's low voice asked from behind.

'It's gorgeous, but why did you change my ticket? It must've cost a fortune.' I said back.

'Does it really matter? You weren't about to fly 15 hours in uncomfortable economy class, with crying kids.' He said softly. Flashing me a smile.

' it's something you should get used to, crying children, stinky diapers.' I said sarcastically, before chuckling. Damon's smile disappeared.

'I'm sorry, did I say something?'

'No, no. Sit down, get comfortable.' He smiled a crooked smile.

The flight passed quickly without any problems. I got some extra work done and spent some time getting to know Damon. He seems like a very down to earth person. His fame hasn't gotten to his head. He did seem kind of down though, but I wasn't about to start asking.

It was another 2 hour drive to get to the house from the airport. The mansion was located right by a lake. It looked like a small castle, it was beautiful.

'It was built in the 19th century by my ancestors, who were a part of the founding families. I think one of my great grandfathers was the mayor at some point. Hence the big house. Me and Stefan used to vacation here all the time with my parents when we were smaller.' He spoke so proudly about his family.

'My family is a founding family in Mystic Falls. My great uncle apparently played a great part in getting rid of the 'vampires' in town. Or so the legends say.' I said with a laugh. We just walked inside, it was even more magical. It was a mix of Italian antiques and a bit if a modern feel. My room was on the first floor, just like the rest of the guest rooms, whereas Damon took the top floor.

The room held a queen size bed in the middle, a big painting framing the beautiful lake outside and a gold chandelier hung from the ceiling. I unpacked and spent the rest of the day talking with my family.

Later that night I had a hard time falling asleep, I made my way to the kitchen in search of some water. But on the way I saw the light in the living room was still on.

Damon sat in a big armchair, in front of an empty bottle of bourbon. His hair was disheveled due to him running his hand through it continuously. His eyes staring out the big french doors that led to the garden.

'Can't sleep?' He asked, acknowledging my presence.

'No, I always have a hard time adjusting to new places. What about you?' I asked curiously, what could make him stay up so late.

'Thinking, how my life got so shitty in a couple of days.' He said sadly.

'You don't have to tell me anything, but if you want to talk I'm right here.' I said with a small smile.

'You're a great person, Lena. You are beautiful, honest.. Not like that bitch Katherine..' I couldn't help but blush at his words. He was a flattering man, no one could resist his blue eyes and raven black hair.

'Is everything alright?' I asked timidly.

'Peachy. My girlfriend cheated on me. Got knocked up. Then decided to make me feel obligated to raise her kid like my own.' He said looking into my eyes.

'But you don't want to?' I asked.

'No way. She ruined us, she can deal with the consequences herself. How about you, how have you been doing?' I never expected Katherine to cheat, not on a man like Damon. He was perfection, they were perfection.

'Well I broke up with my 5 year boyfriend, however it was nothing compared to what you have been through lately.' I said reflecting on Matt appearing at my house the other night.

'I'm sorry to hear that.' He replied.

'We haven't been close for a while, it was kind if expected. Anyway, we should get off that topic, it's too dulling. I want to direct in the future, Tell me something about what it's like to direct a movie.' I replied before moving to sit next to him on the couch. We continued our discussion until we were too tired to speak. I woke up the next morning in my bed, tucked in warmly, a breakfast waiting for me on the bedside table. It was joined by a note written in a elegant script, that said, 'Thank You Lena, you made me forget about all the bad things that happened recently, even if it was just for a while.'

Damon PO

She looked so innocent when she found me in the living room last night. Her brown locks fell lightly against her shoulders. She was wearing a pair of worn out shorts and an old t-shirt. She looked normal, not like Katherine who can't stand to wear anything that isn't Gucci or Chanel she looked beautiful without any makeup. To top it all off she was the only thing that kept me from thinking about that one question, who did Katherine cheat on me with. That's why I couldn't help but make her breakfast the next morning. I never fell back asleep after I carried her to bed that night.

A/N- Damon is really struggling while Elena seems to have moved on, will that turn out to be the perfect antidote for Damon's heartbreak? We finally are starting to have some Delena goodness! Also, Damon is starting to really see Elena as someone more than his personal assistant!


End file.
